New Windsor Holidays from £489

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Your New Windsor Holiday

There's no better way to travel than with one of our holiday packages to New Windsor. The rich history and spectacular views are two of the convincing reasons to spend some time in this captivating city. Dia Beacon, Storm King Art Centre and Ice Time Sports Complex are just some of the attractions you'll want to explore during your trip to New Windsor. A couple of quick clicks is all it takes to put together a tailored New Windsor holiday on Expedia.

Top New Windsor Flight + Hotel Deals

Price found within the past 48 hours. Click for updated prices.
The Crossroads Hotel, Newburgh

The Crossroads Hotel, Newburgh

3 out of 5
per person
26 Sept - 30 Sept
found 1 day ago
Return direct flight included
London (LHR) to Newburgh (SWF)
7.6/10 Good! (464 reviews)
It was quiet but smell of cigarettes even though it’s supposed to be non smoking. The carpets were filthy. Will not stay here again

Reviewed on 1 Jul 2025

Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point

Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point

2 out of 5
per person
3 Sept - 10 Sept
found 1 day ago
Return flight included
London (LGW) to Newburgh (SWF)
8.4/10 Very Good! (1,004 reviews)
We'll be back. Best value rooms.

Reviewed on 13 Jul 2025

Hampton Inn & Suites Newburgh Stewart Airport

Hampton Inn & Suites Newburgh Stewart Airport

2.5 out of 5
per person
27 Aug - 30 Aug
found 19 hours ago
Return flight included
London (LON) to Newburgh (SWF)
9.2/10 Wonderful! (916 reviews)
Decent, clean, environmentally concious

Reviewed on 8 Jul 2025

Homewood Suites Stewart Airport

Homewood Suites Stewart Airport

3 out of 5
per person
27 Aug - 30 Aug
found 19 hours ago
Return flight included
London (LON) to Newburgh (SWF)
9.2/10 Wonderful! (1,001 reviews)
The property was beautiful, the room was exactly as posted but the use of WiFi was challenging at times. I wish there was a better/clearer explanation of where and how to order food. We arrived at the hotel around 8pm and b/c of the WiFi it took us almost 2 hours to order food. Other than that the stay was good.

Reviewed on 13 Jul 2025

New Windsor Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Stewart Intl. Airport (SWF)
Population
8,900
Max Temp Winter
2ºC
Max Temp Summer
27ºC
Top Sights
Bear Mountain State Park, SplashDown Beach and Dia Beacon

Top hotels in New Windsor

Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point
Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point
2 out of 5
915 Union Ave, New Windsor, NY
Fully refundableReserve now, pay when you stay
The price is £100 per night from 17 Jul to 18 Jul
£100
17 Jul - 18 Jul
includes taxes & fees
8.2/10 Very Good! (1,007 reviews)
Great stay
"The staff is so friendly. The Lakeview is amazing. Great to see fireworks on the 4th. The pool area was nice and quiet. Every part of the hotel was clean. I loved our stay here. The hotel room including the bathroom was spacious"

Reviewed on 11 Jul 2025

Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point
Homewood Suites Stewart Airport
Homewood Suites Stewart Airport
3 out of 5
180 Breunig Rd, New Windsor, NY
Fully refundableReserve now, pay when you stay
The price is £145 per night from 21 Jul to 22 Jul
£145
21 Jul - 22 Jul
includes taxes & fees
9.2/10 Wonderful! (1,003 reviews)
"The property was beautiful, the room was exactly as posted but the use of WiFi was challenging at times. I wish there was a better/clearer explanation of where and how to order food. We arrived at the hotel around 8pm and b/c of the WiFi it took us almost 2 hours to order food. Other than that the ..."

Reviewed on 13 Jul 2025

Homewood Suites Stewart Airport
La Quinta Inn & Suites by Wyndham Middletown-Goshen
La Quinta Inn & Suites by Wyndham Middletown-Goshen
3 out of 5
551 Route 211 E, Middletown, NY
The price is £96 per night from 3 Aug to 4 Aug
£96
3 Aug - 4 Aug
includes taxes & fees
9.2/10 Wonderful! (746 reviews)
"I loved this hotel!!! The staff, the hotel itself, the location, everything. We will for sure stay here again"

Reviewed on 11 Jul 2025

La Quinta Inn & Suites by Wyndham Middletown-Goshen
See all 998 properties in New Windsor
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

All Inclusive Holidays

All Inclusive Holidays

Beach Holidays

Beach Holidays

Family Friendly Holidays

Family Friendly Holidays

What to do in New Windsor

Woodbury Common Premium Outlets Shopping Tour from Midtown

Woodbury Common Premium Outlets Shopping Tour from Midtown

£27
per child
96% of travellers recommend
Woodbury Common Premium Outlets Shopping Tour from Midtown
Beacon: Gourmet Beacon Food Tour

Beacon: Gourmet Beacon Food Tour

£98
per adult
Beacon: Gourmet Beacon Food Tour
Taste the Hudson Valley with Gourmet Beacon Food Tour

Taste the Hudson Valley with Gourmet Beacon Food Tour

£100
per adult
Taste the Hudson Valley with Gourmet Beacon Food Tour
See all activities in New Windsor

Frequently asked questions

How much does a New Windsor travel package cost?
Go from wondering to wandering with our New Windsor travel packages, which start from just £489. Pick the hotels and flights that suit your plans. Then, add on one or two experiences or tours to round off your unique escape.
If I'm not able to travel, can I cancel my New Windsor travel package?
Don't worry if you're rethinking your New Windsor travel package --- it's possible to cancel or amend your booking. And if you've booked it within 24 hours, you may be able to do it at no cost. However, bookings made more than 24 hours ago may incur a fee from your hotel, airline or car rental company. We understand life can sometimes throw a spanner in the works, so look up our Customer Service Portal if that happens. When you're ready to make changes, we'll take care of it.
How do I get a cheap travel package to New Windsor?
Combine your hotels and flights, throw in extras such as tours, and save with a New Windsor travel package. You won't just walk away with awesome discounts on your adventure --- you'll have loads of choice at your fingertips too. When you book through Expedia, you can select from more than 550 air carriers and 1,000,000 hotels around the world. Your next big adventure begins right here, right now!
Does Expedia offer Book Now, Pay Later New Windsor holidays?
Expedia has partnered with online lender Klarna to make your next getaway a bit easier on the wallet. Paying in instalments means you can spread the costs of your next adventure, leaving you with more cash to play with while you're away. Klarna has several payment plans to pick from, so you're sure to find one that works with your budget. Take a look at these flexible payment options:

  • Pay monthly holidays: If paying small amounts each month sounds best for you, Klarna offers just that! Paying in easy monthly instalments will make your getaway dreams come true.
  • Pay in instalments holidays: Like the idea of paying off your holiday in multiple transactions? Then select this Book Now, Pay Later option with Klarna.
  • Low deposit holidays: When you spot an unbeatable deal but your budget doesn't quite go that far, Klarna's low deposit holiday plan will help you get what you want.

Where should I stay in New Windsor?
A holiday in New Windsor isn't complete without stopping by New York Military Academy, Mount Saint Marys College Newburgh and Washington Headquarters. Stay close to these sights and make sightseeing easy.
What are the top hotels in New Windsor?
Red Roof Inn & Suites Newburgh -- Stewart Airport in the Vails Gate neighbourhood is a wonderful choice for a New Windsor holiday. Reserve a room here and you'll be well-placed to get out and explore all that this buzzing city has to offer.
How far in advance should I book my New Windsor holiday?
While not all air carriers advertise ticket prices early, you can usually look up international flights on Expedia up to 12 months in advance. This is when you can nab some incredible bargains. If you're booking last minute, there's a chance you could get lucky. Low prices occasionally emerge just weeks prior to departure.
What does an Expedia New Windsor travel package include?
With Expedia, you can choose a combination of flights, hotels and car rentals to build your perfect New Windsor travel package. Once you've made your booking, you can add on fun stuff like tours and experiences. Don't forget, the more you bundle, the more cash you'll save!
What should I know before booking a New Windsor travel package?
An Expedia travel package can be customized for your circumstances and is a simple way to make your money go further. How little or much you include is totally up to you. Rental cars, hotels and flights --- mix and match whatever combination suits your style.
Can I choose my airline with a New Windsor Expedia travel package?
Expedia has access to more than 550 airline partners globally, so you certainly can. Just pick the carrier that suits you and craft the perfect New Windsor escape.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.